Chlorido(1-cyclo-pentyl-idene-4-ethyl-thio-semicarbazidato-κN,S)diphenyl-tin(IV).

The Sn atom in the title compound, [Sn(C(6)H(5))(2)(C(8)H(14)N(3)S)Cl], is penta-coordinated with a trigonal-bipyramidal coordination geometry. The 1-cyclo-pentyl-idene-4-ethyl-thio-semicarbazidate (cpetsc) ligand coordinates through the S atom and the N atom bonds to the cyclo-pentyl group, forming a five-membered ring with the Sn center. The chloride ligand and the coordinated N atom are in axial positions. In the crystal structure, inter-molecular N-H⋯Cl hydrogen bonds form chains along [101].

Related literature

For the biological activity of thio­semicarbazones, see: Dogmak et al. (1946 ▶); Klaymann et al. (1979 ▶); Logan et al. (1975 ▶); Liberta & West (1992 ▶). For their structural characteristics, see: Livingstone (1965 ▶); Akbar & Livingstone (1974 ▶); Campbell (1975 ▶); Padhey & Kauffman (1985 ▶); Haidue & Silverstru (1990 ▶); Huheey et al. (1993 ▶); West et al. (1990 ▶, 1993 ▶); Lobana et al. (2009 ▶). For the anti­tumor activity of organotin(IV) complexes, see: Nath et al. (2001 ▶); Pellerito & n class="Chemical">Nagy (2002 ▶). For related structures, see: Swesi et al. (2005 ▶, 2006 ▶); Valente et al. (1998 ▶); Huheey et al. (1993 ▶); Venkatraman et al. (1999 ▶); Pal et al. (2002 ▶); Teoh et al. (1999 ▶).

Experimental

Crystal data

[Sn(C6H5)2(C8H14N3S)Cl]

M = 492.62

Monoclinic,

a = 8.9031 (9) Å

b = 22.951 (3) Å

c = 11.1381 (11) Å

β = 111.094 (4)°

V = 2123.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.44 mm−1

T = 90 K

0.27 × 0.23 × 0.17 mm

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.698, T max = 0.792

33496 measured reflections

8756 independent reflections

7543 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.062

S = 1.04

8756 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.64 e Å−3

Δρmin = −1.38 e Å−3

Data collection: COLLECT (Nonius 2000 ▶); cell refinement: DEn class="Chemical">NZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809047400/lh2925sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047400/lh2925Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Sn(C6H5)2(C8H14N3S)Cl]	F(000) = 992
Mr = 492.62	Dx = 1.541 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8037 reflections
a = 8.9031 (9) Å	θ = 2.5–34.8°
b = 22.951 (3) Å	µ = 1.44 mm−1
c = 11.1381 (11) Å	T = 90 K
β = 111.094 (4)°	Fragment, colorless
V = 2123.4 (4) Å3	0.27 × 0.23 × 0.17 mm
Z = 4

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	8756 independent reflections
Radiation source: fine-focus sealed tube	7543 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω and φ scans	θmax = 34.8°, θmin = 3.0°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −13→13
Tmin = 0.698, Tmax = 0.792	k = −35→35
33496 measured reflections	l = −17→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.062	w = 1/[σ2(Fo2) + (0.0232P)2 + 1.4419P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
8756 reflections	Δρmax = 0.64 e Å−3
240 parameters	Δρmin = −1.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00150 (18)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Sn1	0.542305 (11)	0.626341 (4)	0.258844 (9)	0.01109 (3)
Cl1	0.25741 (4)	0.662360 (15)	0.18735 (4)	0.01732 (7)
S1	0.58505 (5)	0.680095 (16)	0.45705 (4)	0.01588 (7)
N1	0.80541 (14)	0.60297 (5)	0.38227 (11)	0.0127 (2)
N2	0.88356 (16)	0.63137 (5)	0.49842 (12)	0.0148 (2)
N3	0.86198 (18)	0.69504 (6)	0.64811 (13)	0.0192 (2)
H3N	0.817 (3)	0.7237 (10)	0.660 (2)	0.023*
C1	0.79332 (18)	0.66634 (6)	0.53568 (14)	0.0147 (2)
C3	1.0332 (2)	0.68887 (7)	0.72462 (17)	0.0249 (3)
H3A	1.0694	0.7230	0.7822	0.030*
H3B	1.0951	0.6882	0.6665	0.030*
C4	1.0678 (3)	0.63345 (8)	0.8051 (2)	0.0403 (6)
H4A	1.0173	0.6360	0.8699	0.060*
H4B	1.1844	0.6288	0.8480	0.060*
H4C	1.0241	0.5998	0.7491	0.060*
C11	0.89645 (16)	0.56885 (6)	0.34655 (13)	0.0125 (2)
C12	1.07472 (17)	0.56124 (7)	0.41598 (14)	0.0154 (2)
H12A	1.0983	0.5465	0.5045	0.018*
H12B	1.1324	0.5985	0.4204	0.018*
C13	1.12338 (17)	0.51630 (7)	0.33416 (15)	0.0167 (3)
H13A	1.1191	0.4762	0.3656	0.020*
H13B	1.2333	0.5241	0.3355	0.020*
C14	0.99740 (17)	0.52473 (7)	0.19811 (14)	0.0161 (3)
H14A	1.0232	0.5591	0.1553	0.019*
H14B	0.9901	0.4898	0.1441	0.019*
C15	0.84068 (17)	0.53416 (6)	0.22362 (13)	0.0140 (2)
H15A	0.7610	0.5562	0.1527	0.017*
H15B	0.7927	0.4966	0.2348	0.017*
C21	0.47816 (16)	0.53643 (6)	0.24833 (13)	0.0128 (2)
C22	0.36518 (19)	0.51214 (7)	0.13708 (15)	0.0179 (3)
H22	0.3148	0.5359	0.0636	0.021*
C23	0.3266 (2)	0.45318 (7)	0.13406 (16)	0.0223 (3)
H23	0.2500	0.4368	0.0584	0.027*
C24	0.3997 (2)	0.41813 (7)	0.24138 (17)	0.0215 (3)
H24	0.3732	0.3779	0.2388	0.026*
C25	0.51138 (19)	0.44199 (7)	0.35228 (16)	0.0188 (3)
H25	0.5609	0.4182	0.4257	0.023*
C26	0.55061 (17)	0.50098 (6)	0.35548 (14)	0.0152 (2)
H26	0.6273	0.5172	0.4313	0.018*
C31	0.60608 (17)	0.67142 (6)	0.11590 (14)	0.0140 (2)
C32	0.4852 (2)	0.69413 (7)	0.00748 (15)	0.0183 (3)
H32	0.3754	0.6884	−0.0034	0.022*
C33	0.5245 (2)	0.72517 (8)	−0.08492 (16)	0.0243 (3)
H33	0.4414	0.7401	−0.1586	0.029*
C34	0.6850 (2)	0.73426 (8)	−0.06946 (17)	0.0257 (3)
H34	0.7114	0.7559	−0.1319	0.031*
C35	0.8061 (2)	0.71168 (7)	0.03722 (17)	0.0235 (3)
H35	0.9157	0.7175	0.0475	0.028*
C36	0.76722 (18)	0.68049 (6)	0.12944 (15)	0.0171 (3)
H36	0.8509	0.6652	0.2024	0.021*

	U11	U22	U33	U12	U13	U23
Sn1	0.01215 (4)	0.00957 (4)	0.01273 (5)	0.00074 (3)	0.00592 (3)	0.00121 (3)
Cl1	0.01357 (14)	0.01546 (15)	0.02368 (16)	0.00282 (11)	0.00761 (12)	0.00180 (12)
S1	0.01974 (16)	0.01448 (15)	0.01573 (15)	0.00316 (12)	0.00920 (13)	−0.00064 (12)
N1	0.0134 (5)	0.0116 (5)	0.0126 (5)	0.0001 (4)	0.0042 (4)	−0.0010 (4)
N2	0.0179 (5)	0.0123 (5)	0.0132 (5)	0.0000 (4)	0.0043 (4)	−0.0020 (4)
N3	0.0266 (7)	0.0136 (5)	0.0163 (6)	0.0001 (5)	0.0065 (5)	−0.0036 (4)
C1	0.0210 (6)	0.0101 (5)	0.0132 (6)	−0.0003 (5)	0.0065 (5)	0.0015 (4)
C3	0.0310 (9)	0.0161 (7)	0.0201 (7)	−0.0033 (6)	0.0003 (6)	−0.0042 (6)
C4	0.0507 (13)	0.0213 (8)	0.0283 (9)	−0.0043 (8)	−0.0106 (9)	0.0016 (7)
C11	0.0122 (5)	0.0121 (5)	0.0134 (6)	0.0001 (4)	0.0049 (4)	0.0007 (4)
C12	0.0120 (6)	0.0172 (6)	0.0158 (6)	0.0005 (5)	0.0038 (5)	−0.0010 (5)
C13	0.0131 (6)	0.0202 (7)	0.0182 (6)	0.0029 (5)	0.0073 (5)	−0.0001 (5)
C14	0.0157 (6)	0.0189 (6)	0.0159 (6)	0.0021 (5)	0.0084 (5)	0.0003 (5)
C15	0.0137 (6)	0.0150 (6)	0.0137 (6)	0.0009 (5)	0.0056 (5)	−0.0020 (5)
C21	0.0131 (6)	0.0124 (5)	0.0154 (6)	0.0006 (4)	0.0080 (5)	0.0011 (5)
C22	0.0222 (7)	0.0173 (6)	0.0140 (6)	−0.0023 (5)	0.0065 (5)	0.0006 (5)
C23	0.0302 (8)	0.0199 (7)	0.0187 (7)	−0.0074 (6)	0.0110 (6)	−0.0058 (6)
C24	0.0285 (8)	0.0121 (6)	0.0283 (8)	−0.0029 (5)	0.0157 (6)	−0.0023 (6)
C25	0.0190 (7)	0.0139 (6)	0.0248 (7)	0.0017 (5)	0.0094 (6)	0.0057 (5)
C26	0.0145 (6)	0.0144 (6)	0.0171 (6)	−0.0002 (5)	0.0063 (5)	0.0026 (5)
C31	0.0169 (6)	0.0117 (5)	0.0143 (6)	−0.0002 (5)	0.0070 (5)	0.0000 (5)
C32	0.0214 (7)	0.0174 (6)	0.0153 (6)	0.0010 (5)	0.0056 (5)	0.0017 (5)
C33	0.0334 (9)	0.0227 (7)	0.0167 (7)	0.0036 (6)	0.0090 (6)	0.0058 (6)
C34	0.0388 (10)	0.0217 (8)	0.0233 (8)	−0.0003 (7)	0.0191 (7)	0.0065 (6)
C35	0.0273 (8)	0.0206 (7)	0.0289 (8)	−0.0028 (6)	0.0178 (7)	0.0037 (6)
C36	0.0182 (6)	0.0149 (6)	0.0196 (7)	−0.0015 (5)	0.0085 (5)	0.0017 (5)

Sn1—C21	2.1331 (14)	C14—H14A	0.9900
Sn1—C31	2.1397 (14)	C14—H14B	0.9900
Sn1—N1	2.3123 (12)	C15—H15A	0.9900
Sn1—S1	2.4363 (4)	C15—H15B	0.9900
Sn1—Cl1	2.5095 (4)	C21—C26	1.396 (2)
S1—C1	1.7709 (16)	C21—C22	1.400 (2)
N1—C11	1.2887 (18)	C22—C23	1.394 (2)
N1—N2	1.3909 (17)	C22—H22	0.9500
N2—C1	1.3047 (19)	C23—C24	1.393 (2)
N3—C1	1.3508 (19)	C23—H23	0.9500
N3—C3	1.461 (2)	C24—C25	1.389 (2)
N3—H3N	0.80 (2)	C24—H24	0.9500
C3—C4	1.522 (3)	C25—C26	1.395 (2)
C3—H3A	0.9900	C25—H25	0.9500
C3—H3B	0.9900	C26—H26	0.9500
C4—H4A	0.9800	C31—C32	1.397 (2)
C4—H4B	0.9800	C31—C36	1.403 (2)
C4—H4C	0.9800	C32—C33	1.396 (2)
C11—C12	1.5047 (19)	C32—H32	0.9500
C11—C15	1.505 (2)	C33—C34	1.392 (3)
C12—C13	1.538 (2)	C33—H33	0.9500
C12—H12A	0.9900	C34—C35	1.386 (3)
C12—H12B	0.9900	C34—H34	0.9500
C13—C14	1.539 (2)	C35—C36	1.394 (2)
C13—H13A	0.9900	C35—H35	0.9500
C13—H13B	0.9900	C36—H36	0.9500
C14—C15	1.536 (2)
C21—Sn1—C31	124.36 (5)	C15—C14—C13	102.96 (12)
C21—Sn1—N1	90.12 (5)	C15—C14—H14A	111.2
C31—Sn1—N1	94.09 (5)	C13—C14—H14A	111.2
C21—Sn1—S1	119.41 (4)	C15—C14—H14B	111.2
C31—Sn1—S1	115.63 (4)	C13—C14—H14B	111.2
N1—Sn1—S1	77.54 (3)	H14A—C14—H14B	109.1
C21—Sn1—Cl1	94.66 (4)	C11—C15—C14	102.62 (11)
C31—Sn1—Cl1	96.50 (4)	C11—C15—H15A	111.2
N1—Sn1—Cl1	163.15 (3)	C14—C15—H15A	111.2
S1—Sn1—Cl1	86.050 (13)	C11—C15—H15B	111.2
C1—S1—Sn1	98.75 (5)	C14—C15—H15B	111.2
C11—N1—N2	114.34 (12)	H15A—C15—H15B	109.2
C11—N1—Sn1	124.93 (9)	C26—C21—C22	119.24 (13)
N2—N1—Sn1	120.33 (9)	C26—C21—Sn1	118.99 (10)
C1—N2—N1	115.15 (12)	C22—C21—Sn1	121.77 (10)
C1—N3—C3	121.50 (14)	C23—C22—C21	120.02 (14)
C1—N3—H3N	117.8 (16)	C23—C22—H22	120.0
C3—N3—H3N	117.2 (16)	C21—C22—H22	120.0
N2—C1—N3	118.03 (14)	C24—C23—C22	120.34 (15)
N2—C1—S1	127.40 (11)	C24—C23—H23	119.8
N3—C1—S1	114.56 (11)	C22—C23—H23	119.8
N3—C3—C4	111.85 (16)	C25—C24—C23	119.94 (14)
N3—C3—H3A	109.2	C25—C24—H24	120.0
C4—C3—H3A	109.2	C23—C24—H24	120.0
N3—C3—H3B	109.2	C24—C25—C26	119.85 (14)
C4—C3—H3B	109.2	C24—C25—H25	120.1
H3A—C3—H3B	107.9	C26—C25—H25	120.1
C3—C4—H4A	109.5	C25—C26—C21	120.61 (14)
C3—C4—H4B	109.5	C25—C26—H26	119.7
H4A—C4—H4B	109.5	C21—C26—H26	119.7
C3—C4—H4C	109.5	C32—C31—C36	118.50 (14)
H4A—C4—H4C	109.5	C32—C31—Sn1	119.69 (11)
H4B—C4—H4C	109.5	C36—C31—Sn1	121.78 (11)
N1—C11—C12	125.18 (13)	C33—C32—C31	120.55 (15)
N1—C11—C15	124.34 (12)	C33—C32—H32	119.7
C12—C11—C15	110.35 (12)	C31—C32—H32	119.7
C11—C12—C13	104.07 (11)	C34—C33—C32	120.25 (16)
C11—C12—H12A	110.9	C34—C33—H33	119.9
C13—C12—H12A	110.9	C32—C33—H33	119.9
C11—C12—H12B	110.9	C35—C34—C33	119.81 (15)
C13—C12—H12B	110.9	C35—C34—H34	120.1
H12A—C12—H12B	109.0	C33—C34—H34	120.1
C12—C13—C14	103.78 (11)	C34—C35—C36	120.07 (16)
C12—C13—H13A	111.0	C34—C35—H35	120.0
C14—C13—H13A	111.0	C36—C35—H35	120.0
C12—C13—H13B	111.0	C35—C36—C31	120.82 (15)
C14—C13—H13B	111.0	C35—C36—H36	119.6
H13A—C13—H13B	109.0	C31—C36—H36	119.6
C21—Sn1—S1—C1	89.47 (6)	C31—Sn1—C21—C26	131.64 (11)
C31—Sn1—S1—C1	−82.09 (6)	N1—Sn1—C21—C26	36.61 (11)
N1—Sn1—S1—C1	6.48 (6)	S1—Sn1—C21—C26	−39.13 (12)
Cl1—Sn1—S1—C1	−177.41 (5)	Cl1—Sn1—C21—C26	−127.21 (11)
C21—Sn1—N1—C11	59.16 (12)	C31—Sn1—C21—C22	−48.53 (14)
C31—Sn1—N1—C11	−65.32 (12)	N1—Sn1—C21—C22	−143.57 (12)
S1—Sn1—N1—C11	179.32 (12)	S1—Sn1—C21—C22	140.69 (11)
Cl1—Sn1—N1—C11	165.84 (8)	Cl1—Sn1—C21—C22	52.61 (12)
C21—Sn1—N1—N2	−128.54 (10)	C26—C21—C22—C23	−0.2 (2)
C31—Sn1—N1—N2	106.99 (10)	Sn1—C21—C22—C23	180.00 (12)
S1—Sn1—N1—N2	−8.38 (9)	C21—C22—C23—C24	0.1 (3)
Cl1—Sn1—N1—N2	−21.85 (18)	C22—C23—C24—C25	0.2 (3)
C11—N1—N2—C1	179.64 (13)	C23—C24—C25—C26	−0.3 (2)
Sn1—N1—N2—C1	6.56 (16)	C24—C25—C26—C21	0.2 (2)
N1—N2—C1—N3	179.70 (12)	C22—C21—C26—C25	0.0 (2)
N1—N2—C1—S1	1.32 (19)	Sn1—C21—C26—C25	179.85 (11)
C3—N3—C1—N2	1.9 (2)	C21—Sn1—C31—C32	84.09 (13)
C3—N3—C1—S1	−179.53 (12)	N1—Sn1—C31—C32	177.03 (12)
Sn1—S1—C1—N2	−7.17 (14)	S1—Sn1—C31—C32	−104.83 (11)
Sn1—S1—C1—N3	174.40 (10)	Cl1—Sn1—C31—C32	−16.10 (12)
C1—N3—C3—C4	−80.7 (2)	C21—Sn1—C31—C36	−97.81 (13)
N2—N1—C11—C12	−3.6 (2)	N1—Sn1—C31—C36	−4.86 (12)
Sn1—N1—C11—C12	169.12 (10)	S1—Sn1—C31—C36	73.28 (12)
N2—N1—C11—C15	−178.95 (12)	Cl1—Sn1—C31—C36	162.00 (11)
Sn1—N1—C11—C15	−6.2 (2)	C36—C31—C32—C33	−0.1 (2)
N1—C11—C12—C13	179.96 (14)	Sn1—C31—C32—C33	178.09 (12)
C15—C11—C12—C13	−4.12 (16)	C31—C32—C33—C34	−0.5 (3)
C11—C12—C13—C14	27.08 (15)	C32—C33—C34—C35	0.9 (3)
C12—C13—C14—C15	−39.94 (14)	C33—C34—C35—C36	−0.7 (3)
N1—C11—C15—C14	155.55 (14)	C34—C35—C36—C31	0.1 (3)
C12—C11—C15—C14	−20.40 (15)	C32—C31—C36—C35	0.3 (2)
C13—C14—C15—C11	36.64 (14)	Sn1—C31—C36—C35	−177.83 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···Cl1i	0.80 (2)	2.71 (2)	3.4731 (15)	160 (2)

Table 1

Selected bond lengths (Å)

Sn1—C21	2.1331 (14)
Sn1—C31	2.1397 (14)
Sn1—N1	2.3123 (12)
Sn1—S1	2.4363 (4)
Sn1—Cl1	2.5095 (4)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯Cl1i	0.80 (2)	2.71 (2)	3.4731 (15)	160 (2)

Symmetry code: (i) .